Bis(pyrimidine-2-carboxyl-ato-κN,O)copper(II).

The title compound, [Cu(C(5)H(3)N(2)O(2))(2)], was prepared in a water-ethanol solution containing 2-cyano-pyrimidine, malonic acid and copper(II) nitrate trihydrate. The Cu(II) ion, located on an inversion center, is chelated by two pyrimidine-2-carboxyl-ate anions in a CuO(2)N(2) square-planar geometry. The uncoordinated carboxyl-ate O atom and pyrimidine N atoms are linked to adjacent pyrimidine rings via weak C-H⋯O and C-H⋯N hydrogen bonding. π-π Stacking is observed between nearly parallel pyrimidine rings, the centroid-to-centroid separation being 3.8605 (13) Å.

Related literature

For general background, see: Cheng et al. (2000 ▶); Xu et al. (1996 ▶). For related structures, see: Antolić et al. (2000 ▶ Rodriquez-Dieguez et al. (2007 ▶).

Experimental

Crystal data

[Cu(C5H3N2O2)2]

M = 309.73

Monoclinic,

a = 5.1408 (8) Å

b = 13.2624 (12) Å

c = 7.6735 (11) Å

β = 94.025 (15)°

V = 521.88 (12) Å3

Z = 2

Mo Kα radiation

μ = 2.11 mm−1

T = 291 (2) K

0.32 × 0.20 × 0.16 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.545, T max = 0.722

3167 measured reflections

1196 independent reflections

1068 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.072

S = 1.07

1196 reflections

88 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.42 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807060977/xu2383sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807060977/xu2383Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C5H3N2O2)2]	F000 = 310
Mr = 309.73	Dx = 1.971 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2068 reflections
a = 5.1408 (8) Å	θ = 3.5–25.0º
b = 13.2624 (12) Å	µ = 2.11 mm−1
c = 7.6735 (11) Å	T = 291 (2) K
β = 94.025 (15)º	Prism, blue
V = 521.88 (12) Å3	0.32 × 0.20 × 0.16 mm
Z = 2

Rigaku R-AXIS RAPID IP diffractometer	1196 independent reflections
Radiation source: fine-focus sealed tube	1068 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.016
Detector resolution: 10.0 pixels mm-1	θmax = 27.5º
T = 291(2) K	θmin = 3.1º
ω scans	h = −6→6
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	k = −9→17
Tmin = 0.545, Tmax = 0.722	l = −9→9
3167 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025	H-atom parameters constrained
wR(F2) = 0.072	w = 1/[σ2(Fo2) + (0.0413P)2 + 0.1691P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1196 reflections	Δρmax = 0.25 e Å−3
88 parameters	Δρmin = −0.42 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cu	0.5000	0.5000	0.5000	0.02825 (13)
N1	0.6118 (3)	0.64215 (11)	0.51341 (19)	0.0256 (3)
N2	0.9563 (3)	0.74012 (12)	0.6465 (2)	0.0305 (3)
O1	0.8109 (3)	0.47785 (10)	0.6527 (2)	0.0326 (3)
O2	1.1774 (3)	0.55441 (11)	0.7517 (2)	0.0405 (4)
C1	0.4897 (3)	0.72551 (15)	0.4523 (3)	0.0299 (4)
H1	0.3330	0.7201	0.3847	0.036*
C2	0.5948 (4)	0.81889 (15)	0.4891 (3)	0.0340 (4)
H2	0.5094	0.8774	0.4505	0.041*
C3	0.8314 (4)	0.82293 (14)	0.5852 (3)	0.0352 (4)
H3	0.9074	0.8856	0.6084	0.042*
C4	0.8391 (3)	0.65348 (13)	0.6096 (2)	0.0247 (4)
C5	0.9575 (3)	0.55522 (14)	0.6793 (2)	0.0281 (4)

	U11	U22	U33	U12	U13	U23
Cu	0.02102 (19)	0.02422 (19)	0.0376 (2)	−0.00481 (11)	−0.01119 (13)	0.00144 (12)
N1	0.0194 (6)	0.0268 (7)	0.0296 (7)	−0.0016 (6)	−0.0045 (5)	−0.0006 (6)
N2	0.0276 (7)	0.0265 (8)	0.0361 (8)	−0.0041 (6)	−0.0069 (6)	−0.0030 (6)
O1	0.0252 (7)	0.0260 (6)	0.0445 (8)	−0.0032 (5)	−0.0132 (6)	0.0037 (6)
O2	0.0279 (7)	0.0349 (8)	0.0554 (9)	−0.0024 (6)	−0.0201 (6)	0.0024 (7)
C1	0.0232 (8)	0.0328 (10)	0.0326 (9)	0.0030 (7)	−0.0047 (7)	0.0020 (8)
C2	0.0337 (9)	0.0282 (9)	0.0395 (10)	0.0048 (8)	−0.0027 (8)	0.0030 (8)
C3	0.0403 (10)	0.0250 (9)	0.0395 (10)	−0.0038 (8)	−0.0037 (8)	−0.0029 (8)
C4	0.0194 (7)	0.0270 (9)	0.0270 (8)	−0.0008 (6)	−0.0032 (6)	−0.0026 (6)
C5	0.0244 (8)	0.0281 (9)	0.0308 (9)	−0.0009 (7)	−0.0061 (7)	−0.0013 (7)

Cu—O1	1.9367 (14)	O1—C5	1.281 (2)
Cu—O1i	1.9367 (14)	O2—C5	1.224 (2)
Cu—N1i	1.9714 (15)	C1—C2	1.373 (3)
Cu—N1	1.9714 (15)	C1—H1	0.9300
N1—C1	1.339 (2)	C2—C3	1.378 (3)
N1—C4	1.346 (2)	C2—H2	0.9300
N2—C4	1.319 (2)	C3—H3	0.9300
N2—C3	1.341 (2)	C4—C5	1.520 (2)
O1—Cu—O1i	180.0	C2—C1—H1	119.8
O1—Cu—N1i	96.41 (6)	C1—C2—C3	117.70 (18)
O1i—Cu—N1i	83.59 (6)	C1—C2—H2	121.1
O1—Cu—N1	83.59 (6)	C3—C2—H2	121.1
O1i—Cu—N1	96.41 (6)	N2—C3—C2	122.61 (17)
N1i—Cu—N1	180.0	N2—C3—H3	118.7
C1—N1—C4	117.84 (16)	C2—C3—H3	118.7
C1—N1—Cu	130.04 (13)	N2—C4—N1	125.53 (16)
C4—N1—Cu	111.96 (12)	N2—C4—C5	120.37 (15)
C4—N2—C3	115.95 (15)	N1—C4—C5	114.10 (15)
C5—O1—Cu	115.23 (12)	O2—C5—O1	125.42 (17)
N1—C1—C2	120.31 (17)	O2—C5—C4	120.11 (16)
N1—C1—H1	119.8	O1—C5—C4	114.46 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N2ii	0.93	2.62	3.511 (3)	160
C2—H2···O2ii	0.93	2.39	3.193 (3)	145
C3—H3···O1iii	0.93	2.57	3.336 (3)	140
C3—H3···O2iii	0.93	2.53	3.317 (2)	142

Cu—O1	1.9367 (14)
Cu—N1	1.9714 (15)

O1—Cu—N1

83.59 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N2i	0.93	2.62	3.511 (3)	160
C2—H2⋯O2i	0.93	2.39	3.193 (3)	145
C3—H3⋯O1ii	0.93	2.57	3.336 (3)	140
C3—H3⋯O2ii	0.93	2.53	3.317 (2)	142

Symmetry codes: (i) ; (ii) .